Grasslands across the world are transitioning to woody-dominated states with major consequences for ecosystem service provisioning. Managers have consequently turned to woody plant removal or “brush management” as a tool for grassland restoration. Yet the lifespan of brush management treatments depends on rates of re-encroachment, which are often unknown and seldom considered in restoration planning. In this study, we determine the rate of re-encroachment for Juniperus virginiana L. after 16 yr of fire-based restoration actions in the Loess Canyons Experimental Landscape in Nebraska. In this experimental landscape, reclamation fires are used to collapse J. virginiana woodlands and have been applied almost every yr since 2002 as part of a regional restoration initiative. We observed rapid rates of re-encroachment after fire-based restoration. Seedlings re-established within 1–2 yr and reached densities similar to unburned woodlands in 5–11 yr. Cover was low and stable 8–10 yr after restoration and then transitioned to a rapid growth phase as trees escaped the herbaceous layer. The tallest trees reached heights associated with the onset of seed production after 7–11 yr, marking a demographic transition in the re-encroachment process as restoration sites become sources of seed exposure. These results suggest that single restoration treatments are likely to be short-lived. A key implication is that follow-up J. virginiana treatments are needed to maintain restored grasslands at fairly regular intervals.